Hotels in Ossining

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Check prices for these dates

Tonight
Nov 3 - Nov 4
Tomorrow
Nov 4 - Nov 5
This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

Where to stay in Ossining?

A spacious indoor area with large windows, modern furniture, and a view of a landscaped outdoor area.

1. Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.6 out of 10, Excellent, (281 reviews)
Unwind at this Hudson River retreat with serene views. The cozy café offers breakfast while the fitness center keeps your routine intact. Near Van Cortlandt Manor and Croton Point Park, this hotel provides free WiFi and parking for easy Westchester exploration.
The price is $164
$183 total
includes taxes & fees
Nov 15 - Nov 16
Windrose On Hudson
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is $491
$1,020 total
includes taxes & fees
Nov 4 - Nov 5
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.

3. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
2.5 star property
Hawthorne
8.8 out of 10, Excellent, (1,008 reviews)
This peaceful hotel in Hawthorne offers free breakfast, WiFi, and parking that travelers consistently praise. Take a refreshing swim in the indoor pool or maintain your routine at the 24-hour fitness center. Nearby attractions like Westchester Broadway Theatre make this location ideal.
The price is $148
$169 total
includes taxes & fees
Dec 2 - Dec 3
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
A modern bar area with a bar counter, multiple stools, and a seating area with a sofa and chairs.

4. Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel
4.0 star property
Nyack
8.6 out of 10, Excellent, (1,327 reviews)
Enjoy the relaxing amenities of this JdV by Hyatt in Nyack, featuring a seasonal outdoor pool, fitness center, and terrace. Just minutes from Edward Hopper House Art Center and Buttermilk Falls Park with free WiFi and parking.
The price is $113
$157 total
includes taxes & fees
Dec 2 - Dec 3
Hotel Nyack, a JdV by Hyatt Hotel
A modern kitchen with a central island, bar stools, a fireplace, and a contemporary pendant light.

5. Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County
3.0 star property
Tarrytown
9.0 out of 10, Wonderful, (1,004 reviews)
Enjoy restful nights at this quiet Tarrytown retreat with free WiFi and parking. The on-site bistro serves delicious breakfast and dinner, while nearby attractions like Lyndhurst Mansion await exploration. Clean rooms and helpful staff ensure a comfortable stay.
The price is $152
$174 total
includes taxes & fees
Nov 19 - Nov 20
Courtyard by Marriott Tarrytown Westchester County
A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.

6. Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
Elmsford
8.2 out of 10, Very good, (1,895 reviews)
Escape to this welcoming Elmsford hotel where quiet comfort meets accessibility. Just 10 minutes from Westchester County Center with an indoor pool for morning swims. Nearby highways connect you to attractions while free breakfast, WiFi and parking enhance your relaxing stay.
The price is $133
$152 total
includes taxes & fees
Nov 29 - Nov 30
Baymont by Wyndham White Plains - Elmsford
A spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.

7. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
3.5 star property
Tarrytown
8.4 out of 10, Very good, (1,022 reviews)
Relax in the indoor pool and hot tub after a workout in the 24-hour fitness center at this welcoming Tarrytown hotel. Located near Captain Lawrence Brewing Company, guests appreciate the helpful staff, free WiFi, and convenient parking.
The price is $135
$155 total
includes taxes & fees
Nov 22 - Nov 23
Sheraton Tarrytown Hotel
A spacious room with a stone fireplace, white sofas, and a large window offering a view of the outdoors.

8. Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham
3.5 star property
Tarrytown
7.0 out of 10, Good, (1,023 reviews)
This quiet Tarrytown hotel offers a tranquil courtyard garden and indoor pool for relaxation. Located near Lyndhurst Mansion, with a bistro serving American cuisine, sauna, and 24-hour fitness center for active travelers.
The price is $133
$152 total
includes taxes & fees
Dec 1 - Dec 2
Sleepy Hollow Hotel, a Dolce by Wyndham
A checkered floor, a potted plant, and two metal ladders in a room with large windows.

9. West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
Nyack
7.4 out of 10, Good, (1,509 reviews)
Wake up to complimentary buffet breakfast at this welcoming Nyack hotel before exploring nearby hiking trails or kayaking adventures. Located near Memorial Park and Edward Hopper House Art Center with helpful staff and free WiFi and parking.
The price is $120
$137 total
includes taxes & fees
Nov 4 - Nov 5
West Gate Inn Nyack
A hotel with a modern facade, a prominent signage for SpringHill Suites Marriott, and a covered entrance area with seating.

10. SpringHill Suites by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County
3.0 star property
Tarrytown
8.8 out of 10, Excellent, (1,006 reviews)
Unwind at this welcoming hotel near Tarrytown Music Hall and Lyndhurst Mansion. Start your day with complimentary breakfast before exploring local sites. The 24-hour fitness center keeps routines on track, while friendly staff and free WiFi and parking enhance your stay.
The price is $156
$178 total
includes taxes & fees
Nov 16 - Nov 17
SpringHill Suites by Marriott Tarrytown Westchester County
A spacious lobby with a red sofa, green armchairs, a fireplace, and a staircase leading to an upper level.

11. Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
Mount Kisco
8.6 out of 10, Excellent, (1,003 reviews)
Splash into the seasonal outdoor pool after a day of exploring attractions like Grand Prix New York. This quiet retreat offers dinner at The Hub restaurant, bar service, and helpful staff ready to enhance your stay near Westchester County.
The price is $147
$168 total
includes taxes & fees
Nov 15 - Nov 16
Hotel MTK Mount Kisco
Indoor pool

12. DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1,188 reviews)
Steps from Rockland Bakery and The Shops at Nanuet, this tranquil hotel offers an indoor pool and Windsor Grille for dinner. With a bar, 24-hour fitness center, and free WiFi and parking, enjoy a quiet, relaxing stay near Mahwah Station.
The price is $127
$147 total
includes taxes & fees
Nov 22 - Nov 23
DoubleTree by Hilton Hotel Nanuet
A buffet with various food items, including omelets and baked goods, served in metal containers.

13. Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
2.5 star property
Peekskill
9.2 out of 10, Wonderful, (1,002 reviews)
Wake up to a complimentary breakfast at this Peekskill hotel before exploring Bear Mountain State Park nearby. The indoor pool offers year-round swimming, while free WiFi and parking add convenience. Located near the train station for easy Hudson Valley excursions.
The price is $122
$140 total
includes taxes & fees
Nov 29 - Nov 30
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
An outdoor seating area with wicker chairs and tables, surrounded by greenery and a modern lamp structure.

14. Westchester Marriott

Westchester Marriott
4.5 star property
Tarrytown
8.8 out of 10, Excellent, (687 reviews)
Tucked away in Tarrytown with easy access to major roadways, this hotel offers a peaceful retreat with deep-tissue massages at the onsite spa. Enjoy American cuisine at Crossings Lounge & Bar after a workout in the 24-hour fitness center, all with attentive service from the helpful staff.
The price is $179
$205 total
includes taxes & fees
Nov 22 - Nov 23
Westchester Marriott
A modern kitchen with a large island, bar stools, a flat-screen TV, and a stone backsplash.

15. Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown
3.0 star property
Elmsford
7.8 out of 10, Good, (1,727 reviews)
The price is $113
$129 total
includes taxes & fees
Nov 22 - Nov 23
Hampton Inn White Plains/Tarrytown
A historic stone building with a turret, arched entrance, and a covered patio area.

16. Tarrytown House Estate

Tarrytown House Estate
3.5 star property
Tarrytown
8.2 out of 10, Very good, (1,423 reviews)
Unwind amid lush gardens at this Tarrytown retreat with indoor and seasonal outdoor pools. Goosefeather restaurant serves Asian cuisine after sunset walks on beautiful grounds. Near the train station with free WiFi and parking, just minutes from Lyndhurst Mansion.
The price is $199
$253 total
includes taxes & fees
Nov 8 - Nov 9
Tarrytown House Estate
A snow-covered outdoor area with a stone wall, a metal fence, and a lamp post.

17. Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
7.2 out of 10, Good, (1,000 reviews)
Perched along the Hudson, this inn provides free breakfast, WiFi and parking. Explore nearby Bear Mountain State Park or stroll to Peekskill Landing Park. Rooms include refrigerators and microwaves for added convenience.
The price is $104
$119 total
includes taxes & fees
Nov 8 - Nov 9
Inn on the Hudson
A breakfast area with multiple tables and chairs, a kitchen area with appliances, and a sign for Daybreak Breakfast.

18. Days Inn by Wyndham Elmsford / White Plains

Days Inn by Wyndham Elmsford / White Plains
2.0 star property
Elmsford
7.4 out of 10, Good, (1,032 reviews)
Wake up to free breakfast at this welcoming motel, just minutes from Westchester Broadway Theatre and Lyndhurst Mansion. Guests praise the clean rooms and helpful staff. Enjoy 24-hour fitness, free WiFi, parking, and nearby hiking trails for an effortless stay.
The price is $107
$122 total
includes taxes & fees
Nov 15 - Nov 16
Days Inn by Wyndham Elmsford / White Plains
A spacious hotel lobby with a modern design, featuring a large seating area, a dining table, and large windows providing views of the outdoors.

19. Element by Marriott Spring Valley

Element by Marriott Spring Valley
3.0 star property
Spring Valley
8.8 out of 10, Excellent, (558 reviews)
The price is $134
$156 total
includes taxes & fees
Nov 22 - Nov 23
Element by Marriott Spring Valley
A hotel patio with outdoor seating, a fire pit, and a covered area with glass doors.

20. Residence Inn Orangeburg

Residence Inn Orangeburg
3.0 star property
Orangeburg
8.8 out of 10, Excellent, (1,002 reviews)
Enjoy complimentary breakfast, 24-hour fitness center, and full in-room kitchens at this train station-adjacent hotel. Unwind at the bar after exploring nearby Blue Hill Golf Course or Buttermilk Falls Park, then swim in the heated indoor pool.
The price is $143
$159 total
includes taxes & fees
Nov 29 - Nov 30
Residence Inn Orangeburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Go beyond your typical stay in Ossining

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When is the best time to visit Ossining?

Our prices for hotels in Ossining are cheapest in December

Price trends for hotels in Ossining

Pricing is based on two traveler single night rates
View properties in November
Currently viewing crowd sizes and weather for November.

November

High 11°C / low 3°C. Sunny most days.
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November, no crowd data, average high temperature 11 degrees Celsius, average low temperature 3 degrees Celsius. Sunny most days.
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December, no crowd data, average high temperature 5 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
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January, no crowd data, average high temperature 2 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
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February, no crowd data, average high temperature 4 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
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March, no crowd data, average high temperature 8 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
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April, no crowd data, average high temperature 15 degrees Celsius, average low temperature 6 degrees Celsius. Sunny most days.
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May, no crowd data, average high temperature 21 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 26 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 28 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 24 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 18 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
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Monthly weather averages (˚C)

Top landmarks in Ossining

A dam with a reservoir, surrounded by autumn foliage and hills.

Travelers Rest

If you're looking for things to do when staying in Ossining, go to Travelers Rest.
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Learn more about Ossining

Infamous Sing Sing Prison Museum offers a fascinating glimpse into America's most notorious correctional facility, where history feels eerily present. Louis Engel Waterfront Park provides a refreshing contrast with Hudson River views that make you forget what's just up the hill. The Ossining Historical Society reveals small-town America with unexpected depth and quirky artifacts. Teatown Lake Reservation offers trails where city stress evaporates among pristine forests surprisingly close to New York City. Depot Square buzzes with locals who've perfected small-town conversation while maintaining their metropolitan edge. The Thomas J. Watson Research Center stands as a modernist monument to big thinking in a village balancing prison history with cultural richness.

See all hotels in Ossining
A wooden bridge over a lake with a sign reading "BERGMANN BOARDWALK".

Check out reviews of Ossining hotels guests love

A spacious indoor area with large windows, modern furniture, and a view of a landscaped outdoor area.
Windrose On Hudson

Windrose On Hudson

Windrose On Hudson
Ossining

10/10 Exceptional

This hotel was totally a hidden gem! Absolutely 10 out of 10 the staff was so helpful. The room was beautiful. The grounds were stunning. I’m honestly considering a trip back because I liked it so much.
United States
Nickie
Reviewed October 19, 2026
Windrose On Hudson

Frequently Asked Questions

What accommodations do travelers recommend in Ossining?

Guests like Windrose On Hudson, Tarrytown House Estate and Armoni Inn & Suites.

Can I book refundable accommodations in Ossining?

If you need the flexibility to change your plans to Ossining, most properties provide refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Ossining if I want a vacation rental instead of a hotel?

Browse 8 vacation homes on our site.

What will the weather in Ossining be like during my trip?

The warmest months in Ossining are usually July and August with an average temp of 71°F. January and February are the chilliest months when the average temp is 34°F. The rainiest months are July and October.

Why should I book my Ossining accommodation with Hotels.com?

There are lots of reasons to book your Ossining trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.